New disazo dye.



UNITED STATES PATENT OFFICE.

05C P. Gilli'lllllll ANTI.) LEOIULD H ESSlfi, OI ELBERFELU, (JILRMA NY, [lSSlUN ORS 'lO FAR BEN- JEABRIKEN VORM FRIEDR. BAYER & 00., OF ELBERFELD, GER-MANY, A (llflitl'TlRA/TION OF (rElLh lilNY.

NEW DISAZO DYE Patented Sept. 1 19.03.

Application filed February 19, 1908. Serial No. 416,782.

'1 b all who're it may concern:

Be it known that we, OsoAn GiiN'rnnR and LEOIOLD HEssE, doctors of philosophy, chemists, citizens of the German Empire, residing at Elherlcld, Gcrnmuy, Kingdom of Prussia, have invented new and useful Inipi'ovemcnts in New Disszo C(dOlflllgdllttbtGI', of which the follim'ing is a specification.

This invention rehites to the manufacture and production of new disa zo dyestuffs dye ing cotton from 'violetto blue shades reworkable for their lastness to light. They are obtained by first producing intermediate compounds from the diuzo compounds of the sullurous acid ester of 1.8-ainin0naphtho1 with. suitable enuns to produce intermediate f cou'i'pounds which can be further diczotizcd, eliminating the sulfurous ecid residue from these intermediate compouinls, diazotizin them and combining the thus produced dialzoa zo compounds with derivatives of 2- nmin ii 5-nsphthol 7-sulfonic acid,

The new dyestuffs are in the shape of their alkaline salts dark powders easily soluble in water. Upon reduction with stannous chlorirl and hydrochloric acid the dyestufl's are decomposed 1.8-aminonaphthol, a diamin and derivatives of 2.6-dia1nino5-naphthol-7- sulfonic acid are formed.

In order to carry out this process we can a. g. proceed as follows, the parts being by weight: 223 parts of the sulfurous acidester.

of 1.8--sminonaphthol are dissolved in water and 125 parts of concentratedhydrochloric acid ere added thereto. The sulfurons acid ester i'sthen diszotized with 69 parts of sodium'nitrite at 0 C. and the diazo com pound is added. to an aqueous solution of 187.5 warts of the hydrochlorid of cresidin (Cl-I 1 H OC,H,--1 :3 4). IIOparts of crystallized sodium acetate are gradually introduced into the mixture. The product of the reaction is eciduluted with 'hydrochloric acid and the in'tenn'ediatc compound is preci iitsted by the addition of common salt. tom the resulting azo dycstufl the sulfurous acid residue is eliminated by dissolving the ester in an excess of caustic soda.

and by boiling the solution for some time. The product of the reaction is acidulated with h drochloric acid, filtered ofi, stirred up wit water and the aminoazo compound] is after cooling diazotized with 69 parts 0t sodium nitrate. The diazo compound is then introduced into a solution of 319 parts of Z-amino-5-nq htl1ol-l .7-dlsulfonic acid to which sulilcient sodium carbonate has been added to maintain the mixture alkaline even after the whole oi the dime compound has been added. ilhe dyes-tuft is salted out, pressed and dried. it is, after being dried and pulverized, in tin. shape of its sodium salt adork priawder which is soluble in water with a viol color and wliiich is soluble in concentrate ulfuric acid. with; a blue color. By reducing w ith stennous chlorid and hydrochloric acid l.bzuninonephthol, 1--.in(-:thyl" 2.5(Lll8JlillIIiljl -4 -ethoxybenzene and ld diamino-5ns-phtliol-l .'7-disullonic acid are obtaincd. Tho-new dyestufi' dyes cotton reddish-blue shin] The above described process is carried out in an analogous manner on using other suiir able eunins toproduce thointerinediste con1- pounds on able of being diazotized, such as alpha-nap thylslnin, psraxylidin, metato uidin, acetylamino-ortho-toluidin, 1 -naphthylamin-fi-or 7-sulfonic acid, pars-acetyleminomrtho-nnisidin etc. or other of the above mentioned components to produce the final result, such as 2-diethylam1no-5-naphthol-7-sulfonic acid, 2-phenylamino-5-naphthol-7sul'fonic acid, 2-peratolylamino-5 naphthol-7-sulfonic acid, 2-benzoylimiino-5- naphthol-7-sulfonio acid, 2-ethylztmin0-5- naphthol-7--sulfonic acid, carbonyl-L2-diamino-5-naphthol-7sulf0nic acid, etc.

Having now described our invention and in What manner the some is to be performed,

What we claim as new and desire to secure by Letters Patent is 1. The herein described new zinc-dyestuffs obtainable from sulfurous acid ester of 1.8 aminonaphthol, mnins and with derivatives of 2-amino-5no htholJ-sulfonic acid, which dyestuffs are, a ter being dried and pulverizcd, in the shape of their alkaline salts dark powders'soluble in water, soluble inconcentrated sulfuric acid with from a red to violet to blue color; yielding u on reduction with stsmnous chlorid and hill rochloric acid 1.8-

an:.ino11aphthol,'a-diamin and a derivative of 2.6-diam1no 5na-phthol-7sulfonic acid; and dyeing cotton from violet to blue shades, substantially as hereinbefore described.

2. The herein described new azo-dyestufi obtainable from sulfurous acid ester of 1.8- aminonsphthol,cresidin and with Z-smino-S- Correction i n Letter s'Pa tent No.' 897,529

' naphthol-lJ-disulfonic acid, which dyestui'r' is, after being dried and ulverized, in the shape of its sodium salt a ark owder which is sohible in Water with a vio et color and which is soluble in-concentrated sulfuric acid with a blue color; yieldinil u on reduction LEOPOLD HESSE. Witnesses O rro KoNIG, WM. WASHINGTON BRUNSWICK.

It is herehycertified .that in Letters Pateiit No. 897,529, gran-ted September 1, 1908, upon the application of Oscar Giinther and Leopold Hesse, of Elberfeld, Germany, for an improvement in fNev v Disazc Dyes, anerror appears in the printed specificatioh rei uiring correction, as follows: In'lineIM ge '1, the word nitrate should read nitrite and that the said Lethal-s Patent shouid be read with this correction therein that the same may confcrin to the record of the case in the Patent Oflice Signed and sealed this 8th day of Deeember AQ D., 1908 r c. o. 'BILLINGa Acting Commissioner of Patents. I

substantially as hereinbe- Correction i n Letter s'Pa tent No.' 897,529

' naphthol-lJ-disulfonic acid, which dyestui'r' is, after being dried and ulverized, in the shape of its sodium salt a ark owder which is sohible in Water with a vio et color and which is soluble in-concentrated sulfuric acid with a blue color; yieldinil u on reduction LEOPOLD HESSE. Witnesses O rro KoNIG, WM. WASHINGTON BRUNSWICK.

It is herehycertified .that in Letters Pateiit No. 897,529, gran-ted September 1, 1908, upon the application of Oscar Giinther and Leopold Hesse, of Elberfeld, Germany, for an improvement in fNev v Disazc Dyes, anerror appears in the printed specificatioh rei uiring correction, as follows: In'lineIM ge '1, the word nitrate should read nitrite and that the said Lethal-s Patent shouid be read with this correction therein that the same may confcrin to the record of the case in the Patent Oflice Signed and sealed this 8th day of Deeember AQ D., 1908 r c. o. 'BILLINGa Acting Commissioner of Patents. I

substantially as hereinbe- Av aw.

It is hereby certified that in Letiaers Pateiit No. 897,5 ?9, granted September 1, 1908,

of Elberfeld, New Disazo Dyes, an error appears in the printed specifica- In'line 54, should upon the application of Oscar Giinther and Leopold Hesse, Germany, for an improvement in tiou requiring correction, as follows: page 1, the word nitrate C. O. BILLINGS, Acting Commimlwur of Patentn. 

